Electro-organic synthesis – a 21st century technique
This perspective provides insight into recent electro-organic methods and general trends in this field, and opens up prospects for future viewpoints.
Tuning the stability of organic radicals: from covalent approaches to non-covalent approaches
Covalent and non-covalent approaches to tune the stability of organic radicals through steric effects and the delocalization of spin density.
A happy medium: the synthesis of medicinally important medium-sized rings via ring expansion
Ring expansion strategies are ideally suited to make synthetically challenging, medium-sized rings with much potential in medicinal chemistry.
Silyloxymethanesulfinate as a sulfoxylate equivalent for the modular synthesis of sulfones and sulfonyl derivatives
An efficient protocol for the modular synthesis of sulfones and sulfonyl derivatives has been developed utilizing sodium tert-butyldimethylsilyloxymethanesulfinate (TBSOMS-Na) as a sulfoxylate (SO22−) equivalent.
A copper-catalyzed asymmetric oxime propargylation enables the synthesis of the gliovirin tetrahydro-1,2-oxazine core
The bicyclic tetrahydro-1,2-oxazine subunit of gliovirin is synthesized through a diastereoselective copper-catalyzed cyclization of an N-hydroxyamino ester.
Total synthesis of biseokeaniamides A–C and late-stage electrochemically-enabled peptide analogue synthesis
A late-stage electrochemical decarboxylation enables rapid access to structural analogues of biseokeaniamides A–C, cytotoxic lipopeptide natural products.
Peptide late-stage C(sp3)–H arylation by native asparagine assistance without exogenous directing groups
An efficient method for peptide late-stage C(sp3)-H arylations assisted by unmodified side chain of asparagine (Asn) without any exogenous directing group has been reported.
Programmable synthesis of multiply arylated cubanes through C–H metalation and arylation
Cubane has attracted attention due to its unique 3D structure. Herein, we report the programmable synthesis of multiply arylated cubanes. The developed reaction allows the late-stage and regioselective installation of aryl groups.
Palladium-catalyzed dearomative 1,4-difunctionalization of naphthalenes
The dearomative 1,4-difunctionalization of naphthalenes is achieved by imitating the reactivity of simple conjugated dienes in aromatic systems, providing functionalized spirooxindoles in high yields (up to 99%) with exclusive diastereoselectivity.
Transferring axial molecular chirality through a sequence of on-surface reactions
The axial chirality of reactants is transferred through multistep on-surface reactions to chiral polymers and to prochiral graphene nanoribbons.
Facile access to diverse all-carbon quaternary center containing spirobicycles by exploring a tandem Castro–Stephens coupling/acyloxy shift/cyclization/semipinacol rearrangement sequence
An efficient construction of spirocyclo[4.5]decane derivatives is developed via a Castro–Stephens coupling/1,3-acyloxy shift/cyclization/semipinacol rearrangement sequence.
Sulfoxide-mediated oxidative cross-coupling of phenols
A metal-free, oxidative coupling of phenols with various nucleophiles, including arenes, 1,3-diketones and other phenols, is reported.
Lipshutz-type bis(amido)argentates for directed ortho argentation
Bis(amido)argentate (TMP)2Ag(CN)Li2 was designed as a tool for highly chemoselective aromatic functionalization via unprecedented directed ortho argentation (DoAg).
Controllable double CF2-insertion into sp2 C–Cu bond using TMSCF3: a facile access to tetrafluoroethylene-bridged structures
Copper-mediated controllable double CF2 insertion into sp2 C–Cu bond and subsequent cross-coupling reaction open the door to the synthesis of an array of valuable tetrafluoroethylene-bridged molecules.
Catalytic, transannular carbonyl-olefin metathesis reactions
Transannular carbonyl-olefin metathesis reactions complement existing procedures for related ring-closing, ring-opening, and intermolecular carbonyl-olefin metathesis. This enables molecular editing of steroid-derived frameworks.
Saturated oxygen and nitrogen heterocycles via oxidative coupling of alkyltrifluoroborates with alkenols, alkenoic acids and protected alkenylamines
The oxidative coupling of alkyltrifluoroborates with heteroatom-tethered vinylarenes leads to a broad range of saturated oxygen and nitrogen heterocycles.
Oxidant speciation and anionic ligand effects in the gold-catalyzed oxidative coupling of arenes and alkynes
The mechanism of the gold-catalyzed oxidative cross-coupling of arenes and alkynes has been studied in detail combining stoichiometric experiments with putative reaction intermediates and DFT calculations.
S8-Catalyzed triple cleavage of bromodifluoro compounds for the assembly of N-containing heterocycles
An unprecedented S8-catalyzed selective triple-cleavage of bromodifluoroacetamides is disclosed for the first time.
Direct conversion of phenols into primary anilines with hydrazine catalyzed by palladium
A general and practical method to directly convert phenols into primary anilines with cheap and easy-to-handle hydrazine as the amine and hydride sources catalyzed by Pd/C.
Aromatic C–H amination in hexafluoroisopropanol
We report direct amination of electron-poor arenes and evaluate the crucial factors for the enhanced reactivity in hexafluoroisopropanol.
About this collection
In 2021, Chemical Science welcomed Professor Ning Jiao to the journal as an Associate Editor, handling papers in the area of organic chemistry. Ning has looked back over recent Chemical Science papers and has selected some outstanding articles that he would like to share, including research highlighting optimised total synthesis methodology, cross coupling reactions, and electro-organic synthesis. We hope you enjoy reading through this selection.